Ethanolamine → HCID 23295818, compound

HRID 2291965Notes

Reaction equation

HRID 2291965 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([CH2:14][NH2:15])[OH:13].C(=O)([O-])[O-].[Ca+2]>O1CCOCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:15][CH2:14][CH2:12][OH:13])[CH:7]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 10112Calcium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 23295818HCID 23295818, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,4-difluoronitrobenzene (6.36 g., 40 mmole), ethanolamine (3.04 g., 50 mmole) and calcium carbonate (4 g., 40 mmole) in dioxane (40 ml) was stirred at 80° C. for 1 hour and filtered while hot. The filtrate was diluted with ethyl acetate and washed with H2O and brine. The organic phase was dried over sodium sulfate and evaporated to give a reddish orange solid. Recrystallization from ethyl acetate gave the compound (11) as reddish orange crystals (5.3 g, 66%).

Workup

  1. filtrationfiltered while hot
  2. additionThe filtrate was diluted with ethyl acetate
  3. washwashed with H2O and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated
  6. customto give a reddish orange solid
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5cd472da40e84f1eb0b2d5e6cdd6746d
Source dataset
uspto-grants-1989_01
Patent number
US04799934

Reaction notes

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